A New Synthetic Approach to 8-Chloroflavins and Their Conversion into 8-(Substituted-amino) flavins

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概要

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• Treatment of 5-nitro-6-(N-substituted-anilino) uracils (I) with the Vilsmeier reagent (dimethylformamide-phosphorus oxychloride) gave the corresponding 8-chloroisoalloxazines (8-chloroflavins) (II) in a single step. The conversion of I into II probably proceeds via the intermediate formation of the corresponding isoalloxazine 5-oxides (flavin 5-oxides). In fact, treatment of flavin 5-oxides with the Vilsmeier reagent also gave the 8-chloroflavins. Under the same conditions, 7-bromoflavin 5-oxides did not give the corresponding 7-bromo-8-chloroflavins, but the deoxygenated 7-bromoflavins were obtained. In this case, the Vilsmeier reagent acted as a reducing agent as well as a dehydrating and chlorinating agent. The 8-chloroflavins were converted into 8-(substituted-amino) flavins by treatment with appropriate amines.

• 公益社団法人日本薬学会の論文
• 1980-12-25

著者

• 浜名 政和

  Faculty of Pharmaceutical Sciences, Kyushu University

• 米田 文郎

  Faculty Of Pharmaceutical Sciences Kyoto University

• 浜名 政和

  Faculty Of Pharmaceutical Sciences Kyushu University

• 佐久間 義治

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 佐久間 義治

  Faculty Of Pharmaceutical Sciences Kumamoto University

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